4,7,8-trimethoxyfuro[2,3-b]quinoline

• ChemBase ID: 119320
• Molecular Formular: C14H13NO4
• Molecular Mass: 259.25732
• Monoisotopic Mass: 259.0844579
• SMILES: c12nc3c(c(c1ccc(c2OC)OC)OC)cco3
• Canonical SMILES: COc1ccc2c(c1OC)nc1c(c2OC)cco1
• InChI: InChI=1S/C14H13NO4/c1-16-10-5-4-8-11(13(10)18-3)15-14-9(6-7-19-14)12(8)17-2/h4-7H,1-3H3
• InChIKey: SLSIBLKBHNKZTB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,7,8-trimethoxyfuro[2,3-b]quinoline
• IUPAC Traditional name: skimmianine; 4,7,8-trimethoxyfuro[2,3-b]quinoline
• Synonyms: 4,7,8-trimethoxyfuro[2,3-b]quinoline; Chloroxylonine; Pentaphylline; 7,8-Dimethoxydictamnine; Beta-Fagarine; Skimmianine

Database IDs

• CAS Number: 83-95-4
• PubChem SID: 162107497
• PubChem CID: 6760

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.1843927
• LogD (pH = 7.4): 2.1844711
• Log P: 2.184472
• Molar Refractivity: 68.1626 cm^3
• Polarizability: 28.21399 Å^3
• Polar Surface Area: 53.72 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder

Pharmacology Properties

• Mechanism of Action: Antagonist of 5-hydroxytryptamine receptors; Spasmolytic

Product Information

• Biological Source: Alkaloid from Skimmia japonica and more than 40 other spp. from many genera, mostly in the family Rutaceae
• Application(s): Antiviral; Diuretic; Protozoacide; Spasmolytic agent

REFERENCES

• Delofeu, V. et al., J.A.C.S., 1942, 64, 2326-2338, (isol, Skimmianine)
• Briggs, L.H. et al., J.C.S., 1960, 2458-2460, (ir, derivs)
• Robertson, A.V. et al., Aust. J. Chem., 1963, 16, 451, (pmr, Skimmianine, Evoxine)
• Clugston, D.M. et al., Can. J. Chem., 1965, 43, 2516-2521, (ms, Skimmianine)
• Grundon, M.F. et al., J.C.S. Perkin 1, 1974, 2181-2184; 1975, 302-304, (biosynth, Skimmianine, Evoxine)
• Tillequin, F. et al., J. Nat. Prod., 1982, 45, 486-488, (Skimmianine, haplopine, 7-Isopentyloxy--fagarine)
• Cox, O. et al., Acta Cryst. C, 1989, 45, 1263-1265, (crysts struct, Skimmianine)
• Jackson, G.E. et al., Spectrosc. Lett., 1990, 23, 971-982, (pmr, cmr, Skimmianine)
• Chakravarty, A.K. et al., Phytochemistry, 1999, 50, 1263-1266, (isol, pmr, cmr, ms, Skimmianine)